I founded Endpoint Technologies Associates, Inc., an independent technology market intelligence company, in 2005. Previously, I was vice president of Client Computing at IDC, covering client PCs (desktop and mobile computers). Before that, I ran my own research and analysis firm, directed operations for a developer of multilingual text processing software, ran a technology analysis and publishing practice for a consulting company, managed international accounts for a data communications equipment manufacturer, and did new product development for a computerized trading network. I have published in a variety of forums and been quoted in a number of publications and other media outlets. I snagged a B.F.A. from Bennington College and an MBA from the University of Chicago Graduate School of Business. I am multilingual, world-traveled, and have bicycled over the Alps, but am now a family man.
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It Just Works, NOT! Apple Fail.

As some of you who know me might recall, I sound off on Apple once in a while. Sometimes it ends badly. But I have to speak truth to power from time to time just to clear out the tubes.

The subject at hand here highlights all the ways that Apple’s method — simple, direct, limited choice, intuitive — can blow up in the owner’s face.

Now, I’ve been relatively quiet about this for several years, but a recent incident sent me over the top. It has to do with photo handling in the Apple world, both OS X and iOS, and how broken it is.

The proximal incident occurred when, recently, I opened a photo album on my iPhone called “Swiss Honeymoon” and found in it, along with pictures of my current wife, pictures of my former wife. It just works. Ha!

Another album called “Euro Tour” has pictures of Japan in it.

If this were just the first time I noticed these sorts of anomalies, I would be down to the Apple store to have a genius look the thing over. But I’ve already been to the Apple Store. Twice. With heavy iMac and iPhone in tow. And sat down with the genii for long periods, during which we marveled that such a thing could be happening.

And we tried rebuilding this and that, all to no avail.

So, let’s take it from the top. First of all, a little known or appreciated fact in the tech world is that Microsoft — yes, Microsoft —is much better at handling photos than Apple. Microsoft has had all sorts of trouble convincing people of this fact, and it’s not hard to understand why. If a drooling monster with something green stuck between its teeth came over and sat down next to you to try to convince you that it’s really a very good chess player, you would probably never verify this assertion because you would be fleeing its overpowering odor as fast as possible.

But nonetheless. Aside from fancy ways that Microsoft uses photos in tiles in Windows 8, in search results on Bing, and in megaphoto stitches in SkyDrive, the company just adheres to one simple concept that gives the user control over his or her pix: you can put your photos in whatever folders you want.

So, of course, this structure suits my penchant for knowing where things are. Under My Pictures or Pictures (both, really, because I have the directory synced on multiple machines), I have Family, and under that, Vacations, and under that, the most recent one to Upstate New York, and in that, all the photos from that trip in chronological order. How simple!

What my photo Library looks like on my iPhone: corned beef hash

Apple, on the other hand, has this iron-clad directory in the iPhoto Library. Once you put your pictures in, that’s their order forever and ever. A huge flat file of all your stuff. Which you can view at various scales but not change. Recent updates try to use “Events” as a way to let intelligent software break the directory into chunks that correspond to likely single, well, events. But you can imagine how well that works. Nothing but corned beef hash at the Events level!

Of course, you can use Albums to create the coherent groupings that you want. But that can get tricky as your Library gets large. And it’s cumbersome to create Albums every time you upload photos.

But, as Dr. Seuss would say, “That is not all, oh no! That is not all!”

The real hashing comes when you try to sync iPhoto with the iPhone. That’s when you get the weird honeymoon folder with more than one wife in it. Or the picture of the Buddha at Nara in the middle of the series on the Alps.

The baffled genii could not figure out what was happening. The Mac at least had all the photos, never mind the order. And it was some number like 1,482. The iPhone had only 1,156. And I’m, like, where are the others? The guy fiddled with it for three-quarters of an hour (three genius appointment slots) and got the number on the phone to rise to 1,408. He was, like, well, at least that’s better.

And I’m, like, no! That is not better! If there’s not a one-to-one correspondence between the two, then something is hosed, and I can’t rely on the program (good thing my real photo library is in Windows).

We worked on various levels of reset until we reached one where the genius made me do it (because it could destroy all my data), all for naught.

My own sense is that photo handling was an afterthought for Apple, which was concerned with music when it created iTunes. iPhoto is sort of a bolt on. Between iCloud, iOS, OS X, iPhoto, and iTunes, something is getting lost in the shuffle. And no application of genius seems to make a difference.

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This article is far more like corned beef hash than your syncing problem. You apparently didn’t find the cause of your problem, so you therefore attribute it to something systemic in an entire corporation.

All the king’s horses and all the king’s genii couldn’t put this particular broken software together again. And you’re half right: Windows PC, but iPhone. I know, I know. I should just let Apple drive and everything would be fine. Except that this is a case of Apple on Apple. There are no other systems involved.

I really don’t like how iPhoto opens whenever I attach my iPod. That said, I think you are avoiding reality in favor of gathering the almighty click. Making your own albums is no more difficult than putting your pictures in folders. Grow up.

in iPhoto go to “Preferences” select the “General” icon under “Connecting camera automatically opens” select “No application” (realize that iPhoto uses the word camera to also include an iPod, iPad, iPhone because well…they have cameras) done

Now iPhoto will never try to assist you to import photos from your devices when you connect them. :)

As an additional-somewhat related tip…you can also tell iTunes to not “automatically sync” iDevices when plugged into iTunes. This can be helpful when connecting multiple devices into the same iTunes library.

Thank you for the tip, bc rider, but that fix doesn’t actually solve the problem of the hosed directory. A certain sequence of events created the situation, which certainly contained syncing with multiple devices and various OS upgrades. The problem first occurred after an OS update. So, my thought was that it was a change in iPhoto. But there are a number of moving parts, and at some point, with the defaults set, it went off the rails. I actually don’t care whether I get it back. It’s now more of an artifact, and something I use to import iPhone photos, which I export and move around. I’m just commenting that it’s unusable as is for the basic photo archive.